This invention concerns a series of compounds which exhibit juvenile hormone-like activity. More particularly, this invention is concerned with a series of compounds comprising a long carbon chain containing at least 11 carbon atoms to which is attached a thiophene, benzene or substituted benzene ring.
It is well known to control insects by treating a metamorphic stage of the insect with a juvenile hormone to prevent passage of the insect to a subsequent metamorphic stage. As a result of such treatment the insect will not achieve full maturity. The structure of two such hormones, Juvenile Hormones I and II, are shown below. ##EQU2##
A series of synthetically prepared compounds having juvenile hormone-like activity are described in South African Pat. No. 67/5149. These compounds, like the naturally occurring hormones, have a straight-chain carbon skeleton. This carbon skeleton is terminated by such groups as ester, hydroxy, halo, and amino.
Wigglesworth, J. Ins. Physiol. 9, 105 (1963), reported that dendrolasin exhibits some juvenile hormone activity. Dendrolasin is a naturally-occurring compound secreted by the mandibular gland of the ant. Chemically, it is 9-(2-furyl)-2,6-dimethyl-2,6-nonadiene.
In the course of synthetic studies in the diterpene series Nasipuri et al., J. Chem Soc., 1964, 2146, prepared 9-(3-methoxyphenyl)-2,6-dimethyl-2,6-nonadiene by means of the Wittig reaction. There was no suggestion that the compound possesses biological activity.